1 - (alkyleneiminocarbonyl)-n-(substituted carbamoyloxy)thioformimidates

ABSTRACT

1-(ALKYLENEIMINOCARBONYL)-N-(SUBSTITUTED CARBAMOYLOXY)THIOFORMIMIDATES SUCH AS METHYL 1-(PYRROLIDINOCARBONYL)-N-(METHYLCARBAMOYLOXY)THIOFORMIMIDATE WHICH ARE USEFUL IN PREVENTING THE DESTRUCTIVE EFFECTS OF PESTS SUCH AS INSECTS, TICKS, MITES AND NEMATODES.

United States Patent Int. (:1. C07d 23/06, 27/04, 29/36 U.S. Cl. 260239 E 9 Claims ABSTRACT OF THE DISCLOSURE 1-(alkyleneiminocarbonyl)-N-(substituted carbamoyloxy)thioformimidates such as methyl l-(pyrrolidinocarbonyl) -N- (methylcarbamoyloxy) thioformimidate which are useful in preventing the destructive effects of pests such as insects, ticks, mites and nematodes.

CROSS-REFERENCE TO RELATED APPLICATIONS This application is a division of application Ser. No. 851,531, filed July 9, 1969", now U.S. Pat. 3,658,870, which is in turn a division of application Ser. No. 728,739, filed May 13, 1968, now U.S. Pat. 3,530,220, which is in turn a continuation-in-part of application Ser. No. 647,- 234, filed June 19, 1967, now abandoned.

SUMMARY OF THE INVENTION This invention is a class of compounds of the formula:

wherein R is alkyl of 1 through 4 carbon atoms or alkenyl of 3 through 4 carbon atoms;

R, is alkyl of 1 through 3 carbon atoms, allyl or pro- R is hydrogen or methyl; and

R and R are joined and are alkylene of 2 through 6 carbon atoms.

The background of this invention, and the manner and process of making and using it, are described in US. Pat. 3,530,220, the disclosure of which is incorporated by reference. Some representative compounds of this invention are listed below:

Methyl 1- (aziridinocarbonyl) -N- (methylcarbamoyloxy) thioformimidate Methyl 1- (hexahydro azepinocarbonyl) -N- (methylcarbamoyloxy) thioformimidate Methyl 1- pyrrolidinocarbonyl) -N- (methylcarb amoyloxy) thioformimidate Ethyl 1- pip eridinocarb onyl) -N- allylcarbamoyloxy) thioformimidate p CC Ethyl l- (piperidinocarbonyl -N- (butylcarbamoyloxy) thioformimidate Butyl 1- (piperidinocarbonyl) -N- (methylcarb amoyloxy) thioformimidate Butyl 1- (piperidinocarbonyl) -N- (butylcarb amoyloxy) thioformimidate Methyl l-piperidinocarbonyl-N-(dimethylcarbamoyloxy) thioformimidate The above named compounds are disclosed in Tables II and III which appear in columns 11 through 14 of U.S. Pat. 3,530,220.

I claim:

1. A compound of the formula:

R is alkyl of 1 through 4 carbon atoms or alkenyl of 3 through 4 carbon atoms;

R, is alkyl of 1 through 3 carbon atoms, allyl or pro- R is hydrogen or methyl; and

R and R are joined and are alkylene of 2 through 6 carbon atoms.

2. The compound of claim 1 which is methyl l-(aziridinocarbonyl) N (methylcarbamoyloxy)thioformimidate.

3. The compound of claim 1 which is methyl l-(hexahydroazepinocarbonyl) N (methylcarbamoyloxy)thioformimidate.

4. The compound of claim 1 which is methyl l-(pyrrolidinocarbonyl) N (methylcarbamoyloxy)thioformimidate.

5. The compound of claim 1 which is ethyl l-(piperidinocarbonyl) N (allylcarbamoyloxy)thioformimidate.

6. The compound of claim 1 which is ethyl l-(piperidinocarbonyl) N (butylcarbamoyloxy)thioformimidate.

7. The compound of claim 1 which is butyl l-(piperidinocarbonyl) N (methylcarbamoyloxy)thioformimidate.

8. The compound of claim 1 which is butyl l-(piperidinocarbonyl) N (butylcarbamoyloxy)thioiormimidate.

9. The compound of claim 1 which is methyl l-piperidinocarbonyl N (dimethylcarbamoyloxy)thioformimidate.

References Cited FOREIGN PATENTS 6615725 5/1967 Netherlands 260453 R ALTON D. ROLLlINS, Primary Examiner U.S. Cl. X.R.

260239 A, 239 BF, 293.85, 326.3 

